Plural Azo Groups Attached Indirectly To Each Other By Nonionic Bonding Patents (Class 534/637)
  • Patent number: 5428141
    Abstract: Reactive dyestuffs which, as the free acid, have the following formula ##STR1## in which K is ##STR2## the bonding to the triazinyl radical taking place in each case via the amino function of K, and the remaining substituents have the meaning given in the description, are suitable in particular for the dyeing and printing of natural and synthetic OH- and/or amido-containing materials.
    Type: Grant
    Filed: November 24, 1992
    Date of Patent: June 27, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Josef Herd, Thomas Eizenhofer, Wolfgang Harms, Manfred Hoppe, Wolfram Reddig
  • Patent number: 5420257
    Abstract: A reactive dye comprising a 1,3,5-s-triazine group having a chromophoric group at two of the 2-, 4- and 6-positions and a substituent at the remaining 2-, 4- or 6-position selected from H, optionally substituted alkyl, optionally substituted phenyl, --CH(CO.sub.2 R.sup.1).sub.2, --NR.sup.1 SO.sub.2 R.sup.2, and --SO.sub.2 R.sup.2, wherein each R.sup.1 is H or alkyl and R.sup.2 is alkyl. The reactive dyes may be used for the coloration of textile materials.
    Type: Grant
    Filed: September 17, 1993
    Date of Patent: May 30, 1995
    Assignee: Zeneca Limited
    Inventors: Kenneth Anderton, Andrew P. Shawcross
  • Patent number: 5420255
    Abstract: A process for the continuous reaction of halogenopyrimidines with amines, a halogenopyrimidine and an aqueous amine solution or suspension being passed into a reactor and the reaction product being subsequently conducted away, is described, characterized in that the starting materials are introduced into the reactor simultaneously and continuously with intensive mixing.
    Type: Grant
    Filed: February 22, 1994
    Date of Patent: May 30, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Siegbert Arnold, Hans-Georg Frosch, Manfred Hoppe, Wolfgang Mullers, Richard Sommer
  • Patent number: 5420256
    Abstract: Reactive dyestuffs have the following formula ##STR1## in which D is the radical of an organic dyestuffB is a direct bond or a bridging member on a ring C atom of an aromatic-carbocyclic or on a ring C atom or N atom of an aromatic-heterocyclic ring in D,R.sub.a, R.sub.b, identical or different, are H, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkyl substituted by OH, CN, CO.sub.2 H, OSO.sub.3 H or SO.sub.3 H,U is Cl, F or a pyridinium radical which is unsubstituted or substituted by CO.sub.2 H, CONH.sub.2, SO.sub.3 H or C.sub.1 -C.sub.4 -alkyl,W is straight-chain or branched C.sub.1 -C.sub.6 -alkylene,Y is CH.dbd.CH.sub.2 or CH.sub.2 --CH.sub.2 --X, in whichX is a radical which can be eliminated by alkali,V is H, halogen, C.sub.1 -C.sub.4 -alkoxy, C.sub.1 -C.sub.3 -alkyl, CN, COOH, CONH.sub.2, SO.sub.3 H.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: May 30, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Thomas Eizenhofer, Wolfgang Harms, Karl-Josef Herd
  • Patent number: 5405415
    Abstract: Water-soluble fiber-reactive disazo compounds of the formula (1) given and defined below are described, which compounds serve as dyes for dyeing and printing hydroxy- and/or carboxamido-containing material, in particular fiber material, such as wool and synthetic polyamide and, in particular, cellulose fiber materials, such as cotton. ##STR1## In this formula M is hydrogen or an alkali metal, the groups Y--SO.sub.2 -- and --SO.sub.2 --Y.sup.0 are fiber-reactive groups from the vinylsulfone series, m is 1 or 2, n is zero or 1, R is a group of the formula (2) or (3) ##STR2## in which R.sup.A is lower alkyl which may be substituted, or is phenyl which may be substituted by sulfo, carboxy, lower alkyl and/or lower alkoxy, X is chlorine, fluorine, hydroxy, alkoxy, cycloalkoxy or alkoxy of 3 to 8 carbon atoms whose alkyl radical is interrupted by --O--, --NH--, --CO--NH-- or --NH--CO--, or is benzyloxy, sulfomethoxy, .beta.
    Type: Grant
    Filed: June 23, 1994
    Date of Patent: April 11, 1995
    Assignee: Hoechst AG
    Inventors: Uwe Reiher, Werner H. Russ
  • Patent number: 5403920
    Abstract: Reactive dyes of the formula ##STR1## in which A, U, R.sub.1, R.sub.2, Z and n are as defined in claim 1, are particularly suitable for dyeing or printing cellulosic fibre materials or naturally occurring or synthetic polyamide fibre materials with a high tinctorial yield and produce dyeings and prints with good fastness properties.
    Type: Grant
    Filed: July 19, 1993
    Date of Patent: April 4, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Herbert Klier, Athanassios Tzikas
  • Patent number: 5399674
    Abstract: Fiber-reactive dyestuffs, processes for their preparation and their useDyestuffs of the formula (1) are described ##STR1## The dyestuffs have fiber-reactive properties and dye materials containing hydroxy groups and/or containing carboxamide groups, in particular fiber materials, such as, for example, cellulose fibers, wool and synthetic polyamide fibers, in deep, fast shades by the methods known for this process.
    Type: Grant
    Filed: December 3, 1993
    Date of Patent: March 21, 1995
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jorg Dannheim, Werner H. Russ
  • Patent number: 5391718
    Abstract: Reactive dyes of the formula ##STR1## in which K and Z are as defined in the disclosure, are suitable in particular for the dyeing and printing of cellulose-containing fibre material and produce dyeings and prints having good fastness properties in high coloristic yield.
    Type: Grant
    Filed: February 26, 1993
    Date of Patent: February 21, 1995
    Assignee: Ciba-Geigy Corporation
    Inventors: Athanassios Tzikas, Claudia Carisch
  • Patent number: 5386015
    Abstract: Compounds of the formula ##STR1## and salts thereof, and mixtures of such compounds and salts, wherein F.sub.c is ##STR2## wherein D.sub.1 is an unsubstituted or substituted phenyl or naphthyl diazo component radical,each of Q.sub.1, Q.sub.2 and Q.sub.3 is independently hydrogen or a substituent,each R.sub.5 is independently hydrogen, C.sub.1-4 alkyl or C.sub.1-4 alkoxy,each R.sub.6 is independently hydrogen, halo, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino or --NH--CO--NH.sub.2,R.sub.16 is hydrogen or --SO.sub.3 H,r is 1 or 2, andt is 2 or 3, andb is 1 or 2,whereineach R.sub.1 is independently hydrogen or C.sub.1-4 alkyl,each R.sub.7 is independently hydroxy, C.sub.1-4 alkoxy or --NH.sub.2,each Z is independently ##STR3## and each m is independently 0 or 1.
    Type: Grant
    Filed: July 9, 1993
    Date of Patent: January 31, 1995
    Assignee: Sandoz Ltd.
    Inventors: Paul Doswald, Werner Koch
  • Patent number: 5378817
    Abstract: Reactive dyestuffs of the formula ##STR1## wherein Z=a heterocyclic reactive group and the remaining groups have the meaning given in the description, are outstandingly suitable for dyeing and printing materials containing hydroxyl groups or amide groups.
    Type: Grant
    Filed: January 15, 1993
    Date of Patent: January 3, 1995
    Assignee: Bayer Aktiengesellschaft
    Inventors: Konrad Bootz, Karl-Josef Herd
  • Patent number: 5374301
    Abstract: An ink comprising a liquid medium and a compound of Formula (1) or salt thereof: ##STR1## provided (i) if the compound of Formula (1) has no --SO.sub.3 H groups then it has at least two groups selected from --COOH and --COSH; and (ii) the compound of Formula (1) has at least as many groups selected from --COOH and --COSH as --SO.sub.3 H groups. The inks are useful for ink-jet printing.
    Type: Grant
    Filed: November 30, 1992
    Date of Patent: December 20, 1994
    Assignee: Zeneca Limited
    Inventors: Peter Gregory, Ronald W. Kenyon
  • Patent number: 5359043
    Abstract: A water soluble dye having a reactive group of the formula: ##STR1## wherein: T is a labile atom or group; andR.sup.2 and R.sup.3 are each independently a non-chromophoric optionally substituted aryl or alkyl group.
    Type: Grant
    Filed: April 21, 1992
    Date of Patent: October 25, 1994
    Assignee: Zeneca Limited
    Inventors: Stephen B. Bostock, Michael G. Hutchings, John A. Taylor
  • Patent number: 5359042
    Abstract: New reactive dyestuffs which, in the form of the free acid, correspond to the following formula ##STR1## wherein the substituents have the meaning given in the description, are suitable for dyeing and printing materials containing hydroxyl groups or amide groups, in particular cellulose materials.
    Type: Grant
    Filed: April 29, 1993
    Date of Patent: October 25, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Horst Jager, Frank-Michael Stohr
  • Patent number: 5354849
    Abstract: Anionic disazo compounds of the formula ##STR1## and salts thereof each cation of which is independently a non-chromophoric cation, and mixtures of such compounds or salts, wherein D is whereinR.sub.4 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy or halo,R.sub.1 is hydrogen, C.sub.1-4 alkyl or C.sub.2-4 hydroxyalkyl,R.sub.2 is hydrogen, C.sub.1-4 alkyl, C.sub.1-4 alkoxy, (C.sub.1-4 alkyl)carbonylamino, (C.sub.1-4 alkoxy)carbonylamino or --NHCONH.sub.2,R.sub.3 is hydrogen, halo, C.sub.1-4 alkyl or C.sub.1-4 alkoxy, and ##STR2## wherein R.sub.5 is chloro, hydroxy or --NHCN,R.sub.6 is hydrogen, chloro or cyano, andR.sub.7 and R.sub.8 are as defined in the specification, with the proviso that R.sub.7 and R.sub.8 together contain at least 8 carbon atoms,useful for dyeing or printing anionically dyeable organic substrates such as nitrogen-containing substrates, particularly fiber material comprising natural or synthetic polyamide.
    Type: Grant
    Filed: June 4, 1993
    Date of Patent: October 11, 1994
    Assignee: Sandoz Ltd.
    Inventor: Georg Schoefberger
  • Patent number: 5354850
    Abstract: Water-soluble disazo compounds, a process for their preparation and their use as dyes.Disazo compounds are described which have the formula (1) given and defined below and are used in their function as fiber-reactive dyes for the dyeing of hydroxy- and/or carboxamido-containing fiber material, such as cellulose fiber materials and synthetic and natural polyamide fiber materials, such as wool. They produce brown dyeings and prints having high color strength and good color fastness by the application and fixation methods customary for fiber-reactive dyes ##STR1## in which R is hydrogen or sulfo,R.sup.1 is hydroxy, methoxy or ethoxy,is hydrogen or an alkali metal and the non-fixed sulfo group in the naphthylene radical is in the 6 or 7 position.
    Type: Grant
    Filed: June 24, 1993
    Date of Patent: October 11, 1994
    Assignee: Hoechst AG
    Inventors: Andreas von der Eltz, Werner H. Russ
  • Patent number: 5349057
    Abstract: Water-soluble azo dyes and their heavy metal complex derivatives, such as copper, cobalt and chromium complex azo dyes are described, which have the general formula (1) shown below, have fiber-reactive properties and dye natural and synthetic hydroxyl- and/or carboxamido-containing materials, in particular fiber materials, such as wool and in particular cellulose fiber materials, by the dyeing and printing processes customary for fiber-reactive dyes, in hues which have high color strength and good fastness properties.
    Type: Grant
    Filed: January 10, 1992
    Date of Patent: September 20, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Holger M. Buch, Hartmut Springer
  • Patent number: 5328995
    Abstract: The compounds of the formula ##STR1## where the substituents are as defined in claim 1, are direct dyes for various substrates, in particular cellulosic fibre materials. They are high temperature resistant and therefore are particularly highly suitable for the one-bath, single-stage dyeing of polyester/cotton blend fabrics with a disperse dye for the polyester fibres under the dyeing conditions for polyester fibres.
    Type: Grant
    Filed: January 27, 1993
    Date of Patent: July 12, 1994
    Assignee: Ciba-Geigy Corporation
    Inventors: Rudolf Schaulin, Urs Lauk
  • Patent number: 5319074
    Abstract: A metal-free dyestuff of the formula ##STR1## and metal complex thereof wherein: Fb=the radical of a dyestuff selected from the group consisting of mono- or polyazo, anthraquinone, phthalocyanine, formazan, dioxazine and triphenylmethane radicals,B and B'=a direct bond or an aliphatic or aromatic bridge member to a ring C atom of an aromatic-carbocyclic ring or to a ring C or N atom or an aromatic-heterocyclic ring in Fb,X=CH.dbd.CH.sub.2 or CH.sub.2 CH.sub.2 --Y, whereinY=OSO.sub.3 H, SSO.sub.3 H, OCOCH.sub.3, OPO.sub.3 H.sub.2, OSO.sub.2 CH.sub.3, SCN, NHSO.sub.2 CH.sub.3 --, Cl, Br, F, OCOC.sub.6 H.sub.5, OSO.sub.2 --C.sub.6 H.sub.4 CH.sub.3, ##STR2## R=H or C.sub.1 -C.sub.4 -alkyl, which is optionally be substituted by halogen, hydroxy, cyano, C.sub.1 -C.sub.4 -alkoxy, carboxyl, sulpho or sulphato,Z=a fiber-reactive radical of the formula ##STR3## wherein M=H, C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -thioalkyl, F or CF.sub.
    Type: Grant
    Filed: January 24, 1992
    Date of Patent: June 7, 1994
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfram Reddig, Karl-Josef Herd, Ernst Kysela
  • Patent number: 5310886
    Abstract: There are disclosed azo compounds conforming to formula (1) shown and defined hereinafter, and the preparation thereof. They have fiber-reactive properties and are used for preparing strong and fast dyeings on hydroxy- and/or carboxamido-containing material, preferably fiber material, such as synthetic polyamide, wool and in particular cellulose fibers. ##STR1## where: M is hydrogen or a salt-forming metal,K.sup.o is a radical of the formula (2A) or (2B) ##STR2## where Z is a radical of the formula (3) ##STR3## where R.sup.o is hydrogen or lower alkyl which may be substituted by certain substituents, G is halogen, methoxy, hydroxy or substituted or unsubstituted anilino, Z.sup.1 is a radical of the formula (3a) or (3b) ##STR4##--alk--SO.sub.2 --Yand wherein A, B, R*, R", Y, a, k, D, E and K are as defined in the specification.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: May 10, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Kurt Hussong
  • Patent number: 5306814
    Abstract: A bisazo compound represented by the following formula (I) in the free acid form: ##STR1## wherein R is hydrogen or unsubstituted or substituted C.sub.1 -C.sub.4 alkyl; A is an unsubstituted or substituted phenylene or naphthylene group; Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Y, in which Y is a group capable of being split by the action of an alkali; X is --NR.sub.1 R.sub.2, C.sub.5 -C.sub.7 cycloalkylamino or ##STR2## in which Q is --CH.sub.2 --, --O--, --SO.sub.2 --, --SO-- or --NR.sub.3 -- in which R.sub.3 is hydrogen or C.sub.1 -C.sub.4 alkyl; and n is 1 or 2; R.sub.1 is hydrogen or unsubstituted or substituted alkyl; R.sub.
    Type: Grant
    Filed: December 17, 1992
    Date of Patent: April 26, 1994
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Kingo Akahori, Takeshi Washimi, Takashi Omura, Mahito Fujita
  • Patent number: 5300633
    Abstract: Azo compounds of the formula D.sup.o --N.dbd.N--K.sup.o, in which D.sup.o is a radical of the formula (2), (2a) or (2b) ##STR1## in which Y is a substituent which can be eliminated by alkali to form the vinyl group, X is chlorine or bromine and R is hydrogen, lower alkyl, phenyl or halogen, and K.sup.o is the radical of a coupling component or another radical which contains azo groups, K.sup.o containing a group of the formula --N(R.sup.o)--Z, in which R.sup.o is hydrogen or lower alkyl and Z is a radical of the formula ##STR2## in which A is halogen or cyanoamido, R.sup.20 is hydrogen or lower alkyl, and R.sup.21 has one of the meanings given for R.sup.20, or is an optionally methyl-substituted cycloalkylene radical, or is a phenyl radical, or in which R.sup.20 and R.sup.21, together with the nitrogen atom and if appropriate one or two further hetero groups, can form a 5- or 6-membered heterocyclic radical.
    Type: Grant
    Filed: May 8, 1992
    Date of Patent: April 5, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Jorg Dannheim, Werner H. Russ
  • Patent number: 5298607
    Abstract: The invention provides reactive dyes of the formula ##STR1## wherein D is a mono- or polyazo, metal complex azo, anthraquinone, phthalocyanine, formazane, dioxazine or stilbene dye which contains sulfo groups, R.sub.1 is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sub.2 is hydrogen, methyl or ethyl, X is a radical of the formula --SO.sub.2 CH.sub.2 CH.sub.2 Cl, --SO.sub.2 CH.dbd.CH.sub.2, --SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, --SO.sub.2 CH.sub.2 CH.sub.2 OPO.sub.3 H or --N(R.sub.3)SO.sub.2 CH.sub.2 CH.sub.2 OSO.sub.3 H, and R.sub.3 is hydrogen, methyl or ethyl, and the benzene or naphthalene radical is not further substituted or is further substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.
    Type: Grant
    Filed: May 26, 1993
    Date of Patent: March 29, 1994
    Assignee: Ciba-Geigy Corporation
    Inventor: Herbert Seiler
  • Patent number: 5290922
    Abstract: Disazo compounds which possess fiber-reactive groups and have useful dye properties and are capable of dyeing hydroxyl- and/or carboxamido-containing materials, in particular fiber materials, such as cellulose fibers and natural and synthetic polyamide, such as wool, in strong, fast shades. They conform to the formula ##STR1## wherein the substituents are as defined in the specification.
    Type: Grant
    Filed: December 30, 1992
    Date of Patent: March 1, 1994
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Rolf Gleibner
  • Patent number: 5276148
    Abstract: Reactive dyes of the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,A is unsubstituted or substituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, whereQ is a group which can be eliminated under alkaline reaction conditions,D.sup.1 is phenyl or naphthyl, where these radicals may be substituted,D.sup.2 is phenylene or naphthylene, where these radicals may be substituted, andZ is a reactive radical,with the proviso thata) n is zero when D.sup.1 is substituted by unsubstituted or substituted phenylazo or by unsubstituted or substituted naphthylazo andb) the reactive radical Z is not devised from the triazine series when n is zero and D.sup.1 is dihydroxysulfonylphenyl or trihydroxysulfonylnaphthyl,are used for dyeing and printing organic substrates containing hydroxyl groups or nitrogen atoms.
    Type: Grant
    Filed: May 22, 1992
    Date of Patent: January 4, 1994
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Siegel, Manfred Patsch
  • Patent number: 5268459
    Abstract: Anionic azo compounds which, in the free acid form, have the Formula (1): ##STR1## wherein: Ar and Ar.sup.1 are each independently aryl or substituted aryl providing at least one of Ar and Ar.sup.1 has at least one substituent selected from COOH and COSH;J and J.sup.1 are each independently of formula (2), (3) or (4): ##STR2## each R.sup.5 is independently selected from H, alkyl, substituted alkyl, alkoxy, halogen, CN, ureido and NHCOR.sup.6 ;R.sup.6 is H, alkyl, substituted alkyl, aryl, substituted aryl, aralkyl or substituted aralkyl;each T is independently alkyl;each W is independently selected from H, CN, CONR.sup.10 R.sup.11, pyridinium and COOH;each m is an alkylene chain having 2 to 8 carbon atoms;B is H, alkyl or COOH;R.sup.1, R.sup.2, R.sup.3, R.sup.4, R.sup.10 and R.sup.11 are each independently H, alkyl or substituted alkyl;L is a divalent organic linking group;n is 0 or 1;each X is independently carbonyl or a group of the Formula (5), (6) or (7): ##STR3## Z is OR.sup.7, SR.sup.7 or NR.sup.8 R.sup.
    Type: Grant
    Filed: June 28, 1991
    Date of Patent: December 7, 1993
    Assignee: Imperial Chemical Industries plc
    Inventors: Peter Gregory, Ronald W. Kenyon
  • Patent number: 5268457
    Abstract: Reactive dyes of the formula ##STR1## are particularly suitable for dyeing or printing cellulosic fibre materials by the exhaust method or by continuous processes and give, with a high color yield, dyeings and prints with good fastness properties, in which D is the radical of a monoazo, polyazo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylmethane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dye; R is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by hydroxyl, cyano, carboxyl, sulfo or sulfato; X is fluorine or chlorine; B is a substituted or unsubstituted aliphatic or aromatic bridge member; Y is a substituted or unsubstituted aliphatic, aromatic, araliphatic or heterocyclic radical, which is free from reactive groups; R.sub.2 is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by halogen, hydroxyl, cyano, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.
    Type: Grant
    Filed: December 28, 1992
    Date of Patent: December 7, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 5268458
    Abstract: Azo compounds containing, as the diazo constituent, 1-sulpho-6-carboxy-2-aminonaphthalene and, as the coupling constituent, substances which contain a residue of the pyrimidine or triazine series which reacts with fibers. The azo compounds possess dye properties and, when used in the usual application fixing process for fiber-reactive dyes, color materials containing carbonamide and/or hydroxyl groups, in particular fibrous material such as wool, synthetic nylon and, in particular, cellulose fiber materials in intense, permanent shades.
    Type: Grant
    Filed: June 25, 1992
    Date of Patent: December 7, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Kurt Hussong
  • Patent number: 5256774
    Abstract: Improved reactive dyestuffs have the following formula ##STR1## in which the substituents have the meaning given in the description.
    Type: Grant
    Filed: February 20, 1992
    Date of Patent: October 26, 1993
    Assignee: Bayer Aktiengesellschaft
    Inventors: Wolfgang Harms, Thomas Eizenhofer
  • Patent number: 5243033
    Abstract: Reactive dyes of the formula ##STR1## in which R.sub.1, R.sub.2 and R.sub.3, independently of one another, are C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, ureido, C.sub.1 -C.sub.4 acylamino, carboxyl and sulfo and n, m and p, independently of one another, are the number 0, 1, 2 or 3, X is fluorine or chorine and Z is an aliphatic, araliphatic, aromatic or heterocyclic amino group free from fibre-reactive radicals; or Z is the radical of an aliphatic or aromatic diamine which contains the radical of the formula ##STR2## in which R.sub.1, R.sub.2, R.sub.3, n, m, p and X are as defined, bound via the second amino group; or Z is a radical of the formula ##STR3## in which R.sub.1, R.sub.2, R.sub.3, n, m, and p are as defined; or Z is a radical --NH--SO.sub.2 --(CH.sub.2).sub.2 --OSO.sub.3 H; and the reactive dye of the formula (1) contains at least two sulfo groups, produce, on cellulose fibres, orange dyeings of high color strength and prints of good fastness properties.
    Type: Grant
    Filed: January 13, 1992
    Date of Patent: September 7, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 5243034
    Abstract: Disazo dyestuffs containing sulfo groups and having fiber-reactive properties, which are capable of dyeing materials containing hydroxyl groups and/or carboxamide groups, in particular fiber materials, such as synthetic polyamide fibers, wool and in particular cellulose fiber materials, in deep fast shades. They contain a group corresponding to the formula ##STR1## in which R.sup..alpha. is hydrogen or alkyl having 1 to 4 carbon atoms, which can be substituted by carboxyl, sulfo, cyano, hydroxyl or chlorine;B is fluorine, chlorine, bromine, lower alkylsulfonyl, phenylsulfonyl, methoxy or sulfo;Q is a group of the formula ##STR2## in which Y is vinyl, .beta.-sulfatoethyl, .beta.-halogenoethyl, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl or .beta.-acetoxyethyl,R is hydrogen or lower alkyl,k is the number zero to 4 andX, together with the N atom, forms the bivalent radical of a heterocyclic ring which optionally contains additional hetero atoms.
    Type: Grant
    Filed: November 18, 1991
    Date of Patent: September 7, 1993
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Horst Tappe, Dieter Oehme, Holger M. Buch, Werner H. Russ
  • Patent number: 5241057
    Abstract: Dyestuffs of the formula ##STR1## wherein X=--CH.dbd.CH.sub.2, --CH.sub.2 --CH.sub.2 OSO.sub.3 H, --CH.dbd.CHCl or --CH.sub.2 --CH.sub.2 Cl andY=a fiber-reactive fluoropyrimidinyl or fluorotriazine radical andwhereinu and v=H or SO.sub.3 H, where u.apprxeq.v. Such dyestuffs suitable for dyeing and printing diverse substrates, particularly cotton, to give products a high degree of dyestuff fixation.
    Type: Grant
    Filed: November 1, 1991
    Date of Patent: August 31, 1993
    Assignee: Bayer Aktiengesellshaft
    Inventor: Horst Jager
  • Patent number: 5233026
    Abstract: Reactive dyes of the formula ##STR1## in which D is a monoazo dye, R.sub.1 is hydrogen or a substituted or unsubstituted C.sub.1-4 alkyl radical, Z is an unsubstituted or substituted amino group, and X is a vinyl, .beta.-sulfatoethyl, .beta.-thiosulfatoethyl, .beta.-chloroethyl or .beta.-acetoxyethyl group, with the condition that Z is not a sulfo- or carboxyl-substituted phenylamino group when the triazine radical is bonded to the radical of 1,8-aminonaphthol-3,6- or -4,6-disulfonic acid, and the X--SO.sub.2 radical is bonded directly to an aromatic C atom, are suitable in particular for dyeing and printing cellulose-containing fiber materials by the cold pad-batch method and produce, in high dyeing yields, dyeings and prints having good fastness properties.
    Type: Grant
    Filed: August 2, 1991
    Date of Patent: August 3, 1993
    Assignee: Ciba-Geigy Corporation
    Inventor: Athanassios Tzikas
  • Patent number: 5231171
    Abstract: Reactive dyes useful for dyeing or printing hydroxyl- or nitrogen-containing substrates have the formula ##STR1## where Rg is a radical of the formula ##STR2## Ar is the radical of a benzene or naphthalene ring, Z.sup.1 and Z.sup.2 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, substituted or unsubstituted phenyl, C.sub.1 -C.sub.4 -alkoxy, carboxyl, C.sub.1 -C.sub.4 -alkoxycarbonyl, cyano, halogen or hydroxysulfonyl,Z.sup.3, Z.sup.4 and Z.sup.5 are each hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or substituted or unsubstituted phenyl,U is a group which is detachable under alkaline reaction conditions,X is in case a) the radical of a chromophore or in case b) the radical of a coupling component to which may additionally be attached, via an azo bridge, the radical of a diazo component and which may have additional reactive groups, andL is in case a) a bridge member or in case b) an azo bridge.
    Type: Grant
    Filed: December 13, 1991
    Date of Patent: July 27, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Claus Marschner, Matthias Niedenbrueck, Bernd Siegel, Manfred Patsch, Klaus Pandl
  • Patent number: 5210187
    Abstract: Double attachment reactive dyes have the formula ##STR1## where U.sup.1 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR2## where Q.sup.1 and Q.sup.2 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.3 is a group which is detachable under alkaline reaction conditions,Z is the radical ##STR3## where each Q.sup.4 is independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl which may be substituted by cyano, U.sup.2 is C.sub.1 -C.sub.4 -alkyl, phenyl, C.sub.2 -C.sub.10 -alkenyl or the radical ##STR4## where Q.sup.5 and Q.sup.6 are each independently of the other hydrogen or C.sub.1 -C.sub.4 -alkyl and Q.sup.7 is a group which is detachable under alkaline reaction conditions, and w is 0, 1 or 2,t is 0, 1 or 2,v is 1 or 2 and X and L are each as defined in the description, with the proviso that at least one of the two radicals U.sup.1 and U.sup.2 is not C.sub.1 -C.sub.
    Type: Grant
    Filed: April 9, 1992
    Date of Patent: May 11, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Manfred Patsch, Uwe Nahr, Friedrich Wirsing, Joerg L. Jessen, Klaus Pandl, Claus Marschner, Matthias Dust
  • Patent number: 5200511
    Abstract: Reactive dyes of the formula ##STR1## where m is 0 or 1,A.sup.1 and A.sup.2 are different and each is a fiber-reactive radical or else, in the case of A.sup.2, hydrogen,D.sup.1 and D.sup.2 are substituted or unsubstituted phenylene, substituted or unsubstituted phenylenemethyl, substituted or unsubstituted naphthylene or substituted or unsubstituted naphthylenemethyl,K.sup.1 and K.sup.2 are each the radical of a coupling component of the aminonaphthalenesulfonic acid series andL is a bridge member,are useful for dyeing and printing hydroxyl- or nitrogen-containing substrates.
    Type: Grant
    Filed: March 30, 1992
    Date of Patent: April 6, 1993
    Assignee: Basf Aktiengesellschaft
    Inventors: Hermann Loeffler, Manfred Patsch
  • Patent number: 5197992
    Abstract: A water-soluble reactive dye of the formula:D.sup.1 --Z.sup.1 --NR.sup.1 --T--NR.sup.2 --Z.sup.2 --D.sup.2 (1)whereineach of D.sup.1 and D.sup.2, independently, represents the radical of a water-soluble chromophoric compound,each of Z.sup.1 and Z.sup.2, independently, represents a triazine or pyrimidine residue carrying an atom or group imparting fibre-reactivity to the dye,R.sup.1 represents an optionally substituted alkyl radical,R.sup.2 represents hydrogen or an optionally substituted alkyl radical, andT represents a 1,3- or 1,4-phenylene radical which may carry one or more substituents selected from halogen, alkyl, alkoxy, acylamino, nitro and carboxy.
    Type: Grant
    Filed: January 30, 1991
    Date of Patent: March 30, 1993
    Assignee: Imperial Chemical Industries PLC
    Inventors: John A. Taylor, Duncan A. S. Phillips, Chu K. Yung, Gerard Ellis
  • Patent number: 5196033
    Abstract: A water-soluble reactive dye of the formula:D.sup.1 --Z.sup.1 --NR.sup.1 --T--NR.sup.2 --Z.sup.2 --D.sup.2 (1)whereineach of D.sup.1 and D.sup.2, independently, represents the radical of a water-soluble chromophoric compound,each of Z.sup.1 and Z.sup.2, independently, represents a triazine or pyrimidine residue carrying an atom or group imparting fibre-reactivity to the dye,R.sup.1 represents an optionally substituted alkyl radical,R.sup.2 represents hydrogen or an optionally substituted alkyl radical, andT represents a 1,3- or 1,4-phenylene radical which may carry one or more substitutents selected from halogen, alkyl, alkoxy, acylamino, nitro and carboxy.
    Type: Grant
    Filed: July 9, 1991
    Date of Patent: March 23, 1993
    Assignee: Imperial Chemical Industries plc
    Inventor: John A. Taylor
  • Patent number: 5182371
    Abstract: The reactive dyes have the formula ##STR1## where n is 0 or 1,R.sup.1, R.sup.2 and R.sup.3 are each hydrogen, C.sub.1 -C.sub.4 -alkyl or phenyl,R.sup.4 is fluorine, chlorine, bromine, C.sub.1 -C.sub.4 -alkylsulfonyl, phenylsulfonyl or a radical of the formula ##STR2## L is a bridgemember, A is substituted or unsubstituted C.sub.2 -C.sub.8 -alkylene,Y is vinyl or a radical of the formula --CH.sub.2 --CH.sub.2 --Q, where Q is a group which is detachable under alkaline reaction conditions, andD is phenyl or naphthyl, which may each be substituted.The present dyes are useful in dyeing or printing hydroxyl- or nitrogen-containing fibres.
    Type: Grant
    Filed: February 14, 1992
    Date of Patent: January 26, 1993
    Assignee: BASF Aktiengesellschaft
    Inventors: Bernd Siegel, Manfred Patsch
  • Patent number: 5175260
    Abstract: Disazo dyes suitable for preparing inks have the formula ##STR1## where m is 1 or 2,n is 0 or 1,Z.sup.1 is hydrogen or substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl,Z.sup.2 is hydrogen, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl, C.sub.1 -C.sub.4 -alkanoyl, substituted or unsubstituted benzoyl, C.sub.1 -C.sub.4 -alkylsulfonyl, substituted or unsubstituted phenylsulfonyl or a derivatized 1,3,5-triazinyl radical, andD is the radical of a diazo component of the class of the thiazole, thiophene, aminobenzoic acid or phenylenediamine compounds.
    Type: Grant
    Filed: August 8, 1991
    Date of Patent: December 29, 1992
    Assignee: BASF Aktiengesellschaft
    Inventors: Gunter-Rudolf Schroeder, Udo Mayer
  • Patent number: 5166325
    Abstract: The new polyazo reactive dyestuffs of the formula ##STR1## in which the substituents have the meaning given in the description are highly suitable for the dyeing or printing of hydroxyl- or amido-containing materials. The dyeings and prints obtained are distinguished by high fibre-dyestuff bonding stability and by particularly good stability to oxidizing agents.
    Type: Grant
    Filed: April 25, 1991
    Date of Patent: November 24, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl-Josef Herd, Hermann Henk, Karl-Heinz Schundehutte, Frank-Michael Stohr
  • Patent number: 5118737
    Abstract: A water-soluble dye, free from cellulose reactive groups, of the formula: ##STR1## wherein R.sup.1 is --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H,R.sup.2 is H or --(C.sub.a H.sub.2a O).sub.m (C.sub.b H.sub.2b O).sub.n H, orR.sup.1 and R.sup.2 together with the nitrogen atom form a morpholine ringa and b are different and from 1 to 8m is from 1 to 10;n is from 0 to 9;M is H, ammonium, or a monovalent metal;X (i) NR.sup.1 R.sup.2, (ii) NR.sup.3 R.sup.4, in which R.sup.3 and R.sup.
    Type: Grant
    Filed: June 22, 1990
    Date of Patent: June 2, 1992
    Assignee: Canon Kabushiki Kaisha
    Inventors: Anthony G. W. Baxter, Stephen B. Bostock, David Greenwood
  • Patent number: 5116956
    Abstract: A polyazo compound of the following formula, ##STR1## wherein X is ##STR2## --NR.sub.2 R.sub.3, --OR.sub.4 or --SR.sub.5, in which R.sub.1 is hydrogen or alkyl, R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, alkyl, phenyl, naphthyl or benzyl, A is phenylene, naphthylene or alkylene, Z is a fiber-reactive group of --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a splittable group, Y is pyridinio, and F is polyazo dye moiety carrying a fiber-reactive group like that represented by Z, which compound is useful for dyeing or printing fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.
    Type: Grant
    Filed: May 17, 1990
    Date of Patent: May 26, 1992
    Assignee: Sumitomo Chemical Co., Ltd.
    Inventors: Tetsuya Miyamoto, Kazufumi Yokogawa, Yutaka Kayane, Takashi Omura, Takeshi Washimi, Naoki Harada, Kingo Akahori
  • Patent number: 5112959
    Abstract: A polyazo compound of the following formula, ##STR1## wherein A is phenylene, naphthylene or alkylene, X is --NR.sub.2 R.sub.3, --OR.sub.4 or --SR.sub.5 in which R.sub.2, R.sub.3, R.sub.4 and R.sub.5 are each hydrogen, alkyl, phenyl, naphthylene or benzyl, Z is --SO.sub.2 CH.dbd.CH.sub.2 or --SO.sub.2 CH.sub.2 CH.sub.2 Z' in which Z' is a splittable group, R.sub.1 is hydrogen or alkyl, and F is polyazo dye moiety carrying a fiber reactive group like that represented by Z. This compound is useful for the dyeing or printing of fiber materials to obtain a product dyed or printed in a color superior in various fastness properties with superior build-up property.
    Type: Grant
    Filed: May 22, 1990
    Date of Patent: May 12, 1992
    Assignee: Sumitomo Chemical Company, Limited
    Inventors: Tetsuya Miyamoto, Kazufumi Yokogawa, Yutaka Kayane, Takashi Omura, Takeshi Washimi, Naoki Harada, Kingo Akahori
  • Patent number: 5091515
    Abstract: A new process for the preparation of substituted 2,4-diamino-6-flurotriazines of the formula ##STR1## in which the substituents have the meanings given in the description, comprises reacting ammonium salts of the formula ##STR2## in an aqueous medium at pH values of about 2.5-10 with 2,4,6-trifluorotriazine in a continuous process. The reaction products can be converted to dyestuffs without isolating the intermediates.
    Type: Grant
    Filed: May 3, 1990
    Date of Patent: February 25, 1992
    Assignee: Bayer Aktiengesellschaft
    Inventors: Karl J. Herd, Hans-Georg Frosch, Hermann Henk, Wolfgang Mullers, Frank-Michael Stohr
  • Patent number: 5079347
    Abstract: Disazo compounds conforming to a general formula (1) shown below which have fiber-reactive dye properties and dye hydroxy- and/or carboxamido-containing fiber materials, such as wool and in particular cellulose, in strong fast shades. ##STR1## where R is a hydrogen atom or a sulfo group,R.sup.1 is a hydroxy group, a methoxy group or an ethoxy group,M is a hydrogen atom or an alkali metal,X is a chlorine atom or a fluorine atom,Y is a chlorine atom or an amino group or a group of the general formula (2) ##STR2## where R* is a hydrogen atom or a methyl or ethyl group,n is zero, 1 or 2,R.sup.2 is a hydrogen atom or a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group, andR.sup.3 is a sulfo group or a .beta.-sulfatoethylsulfonyl group or a vinylsulfonyl group,it being possible for R.sup.2 and R.sup.3 to be identical to or different from each other.
    Type: Grant
    Filed: December 6, 1988
    Date of Patent: January 7, 1992
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Holger M. Buch
  • Patent number: 5075428
    Abstract: A dyestuff of the formula ##STR1## in which R is H or Ch.sub.3 ##STR2## in which R.sub.1 is H, substituted or unsubstituted C.sub.1 -C.sub.4 -alkyl or --X--YX is a divalent aliphatic, cycloaliphatic, aliphaticcycloaliphatic radical or an araliphatic radicalY is COOH, SO.sub.3 H, OSO.sub.3 H or SO.sub.2 G, in whichG is CH.dbd.CH.sub.2 or --CH.sub.2 --CH.sub.2 --Z, in which Z denotes a group which can be eliminated under alkaline conditions,R.sub.2 is H or C.sub.1 -C.sub.4 -alkyl, and the benzene radical D and the benzene or naphthalene radical L can contain customary substituents,is suitable for the dyeing and printing of OH- and NH-containing materials. They produce lightfast and wetfast brilliant dyeings and prints.
    Type: Grant
    Filed: July 11, 1989
    Date of Patent: December 24, 1991
    Assignee: Bayer Aktiengesellschaft
    Inventor: Horst Jager
  • Patent number: 5047514
    Abstract: Reactive dyes which contain at least one radical of the formula--SO.sub.2 --CH.dbd.CH.sub.2 (1a)or--SO.sub.2 --CH.sub.2 CH.sub.2 --X (1b)and at least one radical of the formula ##STR1## in which X is an inorganic or organic radical detachable under alkaline conditions, R is hydrogen or substituted or unsubstituted C.sub.1-4 -alkyl, Y is oxygen or sulfur and R.sub.1 is a substituted or unsubstituted aliphatic radical, give dyeings or prints having good fastness properties.
    Type: Grant
    Filed: November 5, 1987
    Date of Patent: September 10, 1991
    Assignee: Ciba-Geigy Corporation
    Inventors: Peter Scheibli, Karl Seitz
  • Patent number: 5021558
    Abstract: Water-soluble fiber-reactive azo, metal complex azo, anthraquinone, phthalocyanine, formazan, azomethine, dioxazine, phenazine, stilbene, triphenylemthane, xanthene, thioxanthone, nitroaryl, naphthoquinone, pyrenequinone or perylenetetracarbimide dyes which contain once or twice the group of the general formula ##STR1## in which: R.sup.x and R.sup.z are, independently of one another, hydrogen or lower alkyl, which can be substituted by halogen, hydroxyl, cyano, lower alkoxy, lower alkoxycarbonyl, carboxyl, sulfamoyl, sulfo or sulfato;W is fluorine, chlorine, bromine, sulfo, phenylsulfonyl or alkylsulfonyl of 1 to 4 carbon atoms;Y is vinyl, .beta.-substituted, .beta.-thiosulfatoethyl, .beta.-phosphatoethyl, .beta.-alkanoyloxyethyl of 2 to 5 carbon atoms in the alkanoyl radical, .beta.-benozoyloxyethyl, .beta.-(sulfobenzoyloxy)ethyl, .beta.-(p-toluenesulfonyloxy)ethyl or .beta.-halogenoethyl.
    Type: Grant
    Filed: March 20, 1990
    Date of Patent: June 4, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventor: Holger M. Buch
  • Patent number: 5010180
    Abstract: Water-soluble azo compounds corresponding to the general formula D--N.dbd.N--K which have advantageous fiber-reactive dyestuff properties and dye materials containing carboxamide groups and in particular materials containing hydroxy groups, such as wool and in particular cellulose fiber materials, in deep fast shades are described.In the formula D--N.dbd.N--K:D is a radical of the general formula ##STR1## in which Y is the vinyl group or an ethyl group in the .beta.
    Type: Grant
    Filed: February 1, 1990
    Date of Patent: April 23, 1991
    Assignee: Hoechst Aktiengesellschaft
    Inventors: Hartmut Springer, Uwe Reiher
  • Patent number: 5006645
    Abstract: Dyes of the formula ##STR1## wherein K is the radical of a coupling component which can additionally contain azo groups, R is hydrogen or methyl, and Z is a fluorine atom, a substituted or unsubstituted amino group, a substituted or unsubstituted hydroxyl group, a substituted or unsubstituted mercapto group, or a substituted or unsubstituted hydrocarbon radical are distinguished by high reactivity and they produce dyeings of good wet- and light-fastness properties. The dyes of the Formula (I) are suitable for dyeing and printing a very wide variety of materials, such as silk, leather, wool, polyamide and polyurethane fibres, and especially cellulosic materials of fibrous structure, such as liner, cellulose, regenerated cellulose, and in particular cotton. They are suitable both for the exhaust method and for dyeing by the pad-dyeing process. They are also suitable for printing, in particular on cotton.
    Type: Grant
    Filed: September 14, 1989
    Date of Patent: April 9, 1991
    Assignee: Ciba-Geigy Corporation
    Inventor: Karl Seitz